Matchmaker Crush

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"Oh, get over it! You can admit it, can't you?! I mean, she is beautiful, and she is kind... How could anyone not have feelings for her? (...) But I guess I will have to let you take the lead here, since that is truly the knightly thing to do for one's partner..."

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Why? Perhaps they felt unworthy and just wanted their beloved to be happy, but in the end just can't resist their own feelings. Or maybe their intentions were pure at the beginning, but the excessive attempts to help their target caused feelings to bloom.

Alternatively/Additionally, the hopeless and lovestruck individual employs the help of the matchmaker to help him/her hook up with the object of their (sometimes superficial) affections...only to later on find themselves falling deeply and genuinely in love with the matchmaker themselves. This usually occurs if the matchmaker and the suitor spend a lot of time together, perhaps practicing how to do the approach or even getting to know their matchmaker a lot better. If this happens, the suitor often reveals later on that his/her feelings have shifted to the matchmaker in question.

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Sometimes overlaps with Wife Husbandry when an older man tries heroically to pair a younger woman off with men her own age, only to fall for her himself.

Examples:

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Anime & Manga

Shakugan no Shana: Hayato Ike often helps Kazumi Yoshida to hook up and show her affection toward Yuji. When he chastises Yuji for leading her on, Yuji confronts Ike about his own feelings for her. It took him until the second season for Hayato to realize it and tries to do anything for himself, for the sake of his feeling toward Kazumi.

Sekai helps Makoto and Kotonoha hook up and puts a lot more effort into it than you would expect. Then she gives herself a reward for her efforts by surprise-kissing Makoto. This does not end well.

There's actually a recursive variant, as Sekai is in turn assisted by her best friend or better said, half-sister Setsuna who also has a crush on Makoto because he protected her from bullies. It turns out that originally Sekai was helping Setsuna try to win Makoto, but developed her own feelings for him and ended up asking Setsuna for help...

CLANNAD: Throughout the Anime series, at every opportunity Kyou tries to push Tomoya to be with her twin sister Ryou, even though she too has a crush on him. And in the Visual Novel, Ryou doesn't even get a real route. Well, she does, but it doesn't count towards the true ending of the story.

Video Girl Ai: Ai falls for Youta, the Unlucky Everydude she's trying to hook up with his female friend Moemi. He, ironically, was trying to hook up said friend with his best friend, Takashi. (And his selfless act is what lets him get Ai's help in the first place...)

Lovely Complex begins with Huge Schoolgirl Risa and The Napoleon Otani trying to be mutual matchmakers for each other. They fail (their respective partners fall for each other and become the Beta Couple), only succeeding to underline to everyone else just how much better they'd do as a couple themselves.

Ryuji and Taiga of Toradora! are another example of mutual matchmakers falling for each other. He was trying to help her get Yusaku's affections, whereas she was supporting him with Minori, and one thing led to another.

Yue Ayase supports her friend Nodoka's feelings for Negi. First, she has no interest in Negi. Then she starts becoming attracted, but suppresses it. Eventually, Yue gets found out and tries to run away in shame, but Nodoka tell her that it's okay for both of them to have feelings for Negi and that they're still friends. Additionally, Nodoka soon comes up with an interesting solution that embarasses her.

Haruna aka Paru plays with this, she's acting as matchmaker for both Yue and Nodoka. After Negi's battle in the Ostian tournament she declares she has fallen for him... then laughs, declares she was kidding, and gets yelled at for her joke.

Akira Ookochi, who asked Negi directly to go the Pactio route with Ako, Makie and Yuuna(Ako and Makie both like Negi, while Yuna needs the Pactio to follow in her mother's footsteps) but refused to get one for herself. Until a long while later. Lampshaded by Chamo right before the last fact happens.

The Korean manhwa Green Boy has a more direct spin on this. Ha-Eun has a crush on Taejin, who is already on crushing on Jae-in. Since Ha-Eun wants to be friends with both Jae-in and Taejin, she happily pushes them both toward each other even as she makes no secret about her crush on Taejin to both of them while assuring them that she'd never act on it because she finds them both adorable together. The trope is played with, however, when later chapters show that this is partly a facade, and she visibly struggles to stifle her Green-Eyed Monster the first time she sees them kiss.

Sakuya gave up her own spot in a high-class school so that her childhood friend Wataru could go to the same school as another childhood friend, Isumi, he has a crush on. She also loudly complains about his lack of progress in confessing his feelings to Isumi. A lot of the Ship Tease in the later chapters, however, suggest very strongly that Sakuya has a crush on Wataru herself.

Akane in Suika eventually regrets that she set up Touko and Yoshikazu.

In Maid-Sama!, Aoi ships Usui/Misaki, but recently realizes he likes Misaki too. Despite this, he is genuinely happy for Misaki's relationship with Usui because being with him makes her look "cuter," and Aoi likes it when Misaki looks cute.

Inverted in Chihiro's arc. When Keima needs to capture Chihiro, he helps her capture her crush (after all, she just needs to fall in love, it doesn't have to be with Keima), but she eventually skips the confession to be with Keima instead.

A few arcs later, Keima recruits Chihiro's friend Ayumi to help him recapture Chihiro to determine which of them is Mercury's host. Ayumi accepts to help him and does a good enough job at feigning disinterest that Keima comes to the conclusion that she doesn't have feelings for him and has no goddess. He was wrong.

Another example would be Tenri's goddess, Diana. Since Tenri is too shy to come forth with her feelings for Keima, Diana tries to push her towards him and eventually falls for Keima herself.

Yukari, a bisexual girl from the manga Rosario + Vampire, is this for both Tsukune and Moka, who she openly ships together. This is because Yukari's in love with both of them, and she thinks that if they become a couple, it'll be easier for her to get a threesome with them.

Takeo from My Love Story!! tries to hook up his friend Suna with Yamato, however he's fallen for her. He decides to cheer their 'romance' on nevertheless. The problem is Yamato likes Takeo, not Suna, but Takeo is Oblivious to Love. It takes Suna outright telling them that the other likes them for the two to become a couple.

Tenga from Kiznaiver tries to set up Chidori with Katsuhira. It's revealed in episode 8 that Tenga has developed feelings for Chidori.

Sophia in My Next Life as a Villainess: All Routes Lead to Doom! is at least a little in love with her best friend Katarina, but unlike everyone else she seems more interested in getting her to date her older brother Nicol. Given how much she thinks of her brother that says a lot. With her advice, Nicol is the only one to manage so successfully get her to accept a girly gift like a necklace by making sure it's not too expensive and resembles one from a story Katarina likes.

When the two protagonists of Your Name are switching bodies, Mitsuha will try to help Taki to get closer to his crush, Miki Okudera, eventually setting up a date between them. However, Mitsuha gradually falls in love with Taki, even visiting Tokyo in order to wish him good luck, not realizing their time is out of sync. Taki on the other hand also falls in love with her, with Miki seeing this when he doesn't seem to be interested in their date.

In Dad, the Beard Gorilla and I, Yukari wants to pursue Souichi, and she is helped by Tsukasa and Hino, who give her tips on how to attract his attention, and try their best to find opportunities for the two to get together. Eventually, Tsukasa falls for Souichi, while Hino becomes attracted to Yukari. The first pair becomes an Official Couple, while the second gets a Maybe Ever After after the former gets married.

Pokémon: During a mini-arc in the Galactic Battles season, Guest-Star Party Member Lyra tries to pair her friend Khoury up with Dawn. But over time, Lyra comes to realize she may have feelings for Khoury herself.

Marcie trying to set up Charlie Brown and Peppermint Patty, while liking Charlie Brown herself.

Linus trying to set up Charlie Brown and the Little Red-Haired Girl, but turning out to like her himself (unfortunately for Charlie, Linus is way smoother than he is).

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Fan Works

Variant in Advice and Trust. Both Shinji and Asuka had a crush on Rei before starting playing matchmaker, but since they were dating and not willing to share, they decided to look for someone who was good enough for her.

A brief subplot in When Harry Met Sally... finds Harry and Sally setting each other up with each other's best same-gender friends. Unfortunately, said friends hit it off immediately with each other, leaving Harry and Sally to continue to deal with their own feelings.

French Kiss: Luc starts out trying to help Kate win back her ex-fiance Charlie, but falls for her in the process. Somewhat subverted in that he doesn't realize this until after the plan succeeds.

In the movie Roxanne, the articulate fire chief "C.D." helps a much younger fireman Chris, hook up with a bright, beautiful astronomer (Roxanne), by writing love letters for him to give to her. He finds he has fallen for Roxanne as well.

In American Pie 2, Michelle helps Jim get Nadia, the girl he's always been in love with, only to find that she's fallen in love with him.

He's Just Not That into You sort of has this. Justin Long's character doesn't realize he loves Gigi, the girl he was teaching about men and dating, until after he turns down her advances (she had a crush on him, mistaking his kindness for interest. Subconscious attraction?).

The Ugly Truth: The lead characters start to get along when he helps her get together with the guy she likes. Of course, then the two start falling for each other...

In What's Your Number?, Colin falls in love with Ally while he's helping her track down her ex-boyfriends to see if any of them are worth taking a second look at.

In Now You See Me, Merritt takes delight in using his cold reading skills to uncover the romantic history and continuing attraction between Danny and Henley, apparently hoping they'll eventually get (back) together... but is not above hitting on Henley himself when he sees she's getting nowhere with Danny.

Literature

Memoirs of a Geisha has the Chairman heroically giving up Sayuri to his friend Nobu until he discovers Sayuri has been in love with him for years. Interestingly, we don't actually find out he loves her (though there are hints) until almost the end of the book.

Emma shows the one way to make this scenario more awkward: Emma tries to hook up Mr. Elton with her best friend Harriet. The result is Mr. Elton falling for Emma!

In a similar Jane Austen example, Edmund Bertram of Mansfield Park spends some time shipping his future wife (and cousin) Fanny Price with Henry Crawford.

Only In The Movies combines this with Playing Cyrano. Vanni, a bright but unattractive girl plays Cyrano for her close friend Jake, despite having a huge crush on him. Don't worry: he figures it out eventually.

In the Dragonriders of Pern novel The White Dragon, we find Masterharper Robinton has strong feelings for his gifted apprentice Menolly, even though he has done everything he can to foster a romantic attachment between her and Sebell. In a moment of weakness, he kisses her and finds, to his surprise, Menolly feels the same way, although the immense age difference (implied to be 40 years or more) makes a romantic involvement a non-starter.

In an L. M. Montgomery story "The Education of Betty", a man, having been the best man while his best friend marries his true love, then did his best for the widow and orphan. When the girl is grown up, he tries to pair her with a man his own age, and demands to know why she refused — whereupon she declares her love. Prior to that, his awareness had been limited to realizing that her mother was not so perfect after all, lacking her daughter's spirit.

In As You Wish by Jackson Pearce, the jinn that appears to Kayla is supposed to grant 3 wishes to her as quickly as possible, as per protocol. One of her wishes is to date the most popular guy in school, and the jinn starts to fall in love with her after she wishes this.

In Middlesex, this happens with Desdemona and Lefty. Although Lefty was in love with her before she started trying to matchmake for him. It's only during the matchmaking process, however, that the feels start to become more reciprocal.

Friends: Rachel made this mistake twice with Ross. First, she initially agrees to Phoebe setting Ross up with a "bald" girl before finding out that said girl has grown her hair back and is beautiful. Second, she begs Ross to take Emily (her boss's niece) to the opera so she can meet up with Joshua, but then starts having feelings for Ross again when he and Emily are getting married.

Skins does this in the S4 finale; Katie is trying to get Thomas and Pandora back together, but realises at a fairly awkward moment that the plan has gone badly wrong and she's fallen for him...

In Charmed, Coop, a cupid who's job it is to find true love for people, falls in love with his charge, Phoebe.

In Gossip Girl, Chuck spends the first half of Season 1 trying to help his friend Nate have sex with Blair. And then the second half trying to prevent them having sex.

On Home and Away, Rachel has twice set her coworker Julie up with her male friends, only to discover that said friends were more interested in her. This was previously done to Rachel, when Dan and Leah tried to set her up with Peter only to discover that Peter was in love with Leah.

On How I Met Your Mother Robin finds that after she sets up Barney with Nora, she wants him back herself.

On Misfits, Rudy spends all of Series 4 and the beginning of Series 5 trying to get Jess to go out with Finn. Rudy being Rudy, it's fairly inevitable that he eventually ends up falling for her himself and going to extreme and comical lengths to ensure everyone gets a happy ending. Making a video of Jess on the loo so that Finn will see her at her most unattractive, accidentally posting it to YouTube instead of texting it to Finn, then knocking her phone into a lake before she can watch - only to have her see it later anyway on someone else's computer, because that's how the Internet works - is actually one of the less disastrous things he does. Luckily it all works out... eventually.

Inverted on That '70s Show. Red tries to set Eric up with their coworker Stacey, but when he tries to talk Eric up to her she makes a pass at Red himself.

Community: Played with in "Herstory of Dance." Shirley and Annie both try and set Abed up with dates, and Abed thinks it will be fun to invoke the Two-Timer Date trope (without telling Shirley, Annie, or the dates). At the beginning of the night, he meets a girl named Rachel at the coat check, who thinks his plan sounds awesome and decides to help. Throughout the night, Rachel and Abed are getting closer, but he fails to notice and accidentally offends her. He goes back to apologize, and admits he really should have noticed.

Abed: I was so caught up in the obvious trope that I missed the even more obvious one.

In Power Rangers Zeo, when Tommy receives a "Dear John" Letter from Kimberly and gets heartbroken, Katherine tries to help him hook up with a girl named Heather, who seems the perfect match for him. Her attempts only result in Tommy becoming attracted to Kat herself, which coupled with the fact she already harbored feelings for him from the past season result in the two getting together.

Music

The legend of the star-crossed lovers Diarmuid and Deirdre in Irish mythology (below) was set to music by Irish folk-rockers the Horslips as the ballad Warm Sweet Breath of Love. The opera Tristan und Isolde sets the whole tale to music.

Myths & Religion

The legend of the star-crossed lovers Diarmuid and Deirdre in Celtic Mythology. The valiant and noble warrior Diarmuid is sent by his King to collect the lovely Deirdre, the fairest woman in all Ireland, for her arranged marriage to the King Diarmuid serves. The King explains that he can only trust Diarmuid to be principled enough to ensure the beautiful woman arrives safely, and still a virgin. However, she is less than thrilled at being married off to a man twice her age. Romance begins and the two elope as lovers, enraging the king who sends warriors to track and slay them.

This is further complicated if one takes into account the other versions of the legend in which Diarmuid is cursed with a spot on his skin that entrances any woman who sees it; which is what happened with Deidre who magically forces him to run away with her, though Diarmuid did come to genuinely love Deidre in time.

This was later incorporated wholesale into the Arthurian mythos as the tale of Tristan and Isolde. Here, the added twist is that hearing of her revulsion for King Mark of Cornwall, Tristan acquires a love potion, which with the best of intentions he intends using on her to make her fall in love with Mark. But she deftly ensures Tristan drinks it so he falls in love with her...

Viola in Twelfth Night ends up Playing Cyrano when she's disguised as a boy and the man she's fallen in love with sends her to the girl he likes with love messages. Then the girl falls in love with her....

Julia in Two Gentlemen of Verona, worried about her love interest who's been away, disguises herself as a boy and follows him. To her dismay, she finds him running after a different girl, and when he doesn't recognize her in her disguise she ends up delivering a love note for him.

Launcelot in The Merchant of Venice is the go-between for Lorenzo and Jessica, delivering their love messages and generally helping them with their elopement. However, he's fond enough of Jessica that many productions interpret their relationship this way. Lorenzo himself can't help but wonder, at one point joking that he'll get jealous if Launcelot keeps stealing Jessica for alone time.

Averted in Much Ado About Nothing, though the villain of the play briefly convinces Claudio that this is in play between the Prince and Hero. Don Pedro the Prince is also sometimes interpreted as being so interested in the match he makes between Beatrice and Benedick because he's in love with Beatrice himself.

In the opera La Gioconda, the main character Gioconda is in love with the rebel Enzo. However he's in love with the noblewoman Laura, who saved Gioconda and her mother at the beginning. Gioconda decides to repay her debt to Laura by helping her escape from her loveless marriage and get together with Enzo, even giving her life to do so.

Video Games

Quoted above: Sain from Fire Emblem: Rekka no Ken tells such phrases to his best friend and partner Kent in their B support, having noticed Kent's Bodyguard Crush on their common lady of liege Lyndis, whom he also has a crush on. (Then again, this isSain we're talking about.)

This can also potentially happen to Arthur, shall the player unlock his supports with Princess Camilla who is in love with the Player Character. Again, if their S-Support is unlocked Arthur will tell Camilla about his feelings, and she will tell him that she has come to like him back.

In Tokimeki Memorial, your best friend (alias, the main guy's friend) Yoshio Saotome is always ready to help out with tips about the girls in the game. However, he might have feelings for one of these ladies as well... Lucky for you, he's more likely to fall for your girl's best friend (i.e.: if you woo Shiori, he may hook up with her best friend Megumi) than fight you. In the radio drama canon, in fact, he's seen dating the local Meganekko, Mio Kisaragi.

Tokimeki Memorial 2 has Kotoko Minaduki, who wishes for her best friend, Hikari (the heroine, and main love interest of the protagonist) to finish with her childhood friend of a protagonist. Being a solid Type A Tsundere, she will NOT hesitate giving Armor Piercing Slaps to him if she ever feels he neglects Hikari. Yet the protagonist can woo Kotoko (much to her resistance to her growing feelings for him), leading to this trope, and a Slap-Slap-Kiss (coming all from Kotoko) on Kotoko's ending, where she and Hikari are in love with the protagonist.

In Final Fantasy VII's romance subplot, Tifa begins to like Cloud more when he shows concern for her friend and potential love rival Aerith. It can easily be seen as Tifa appreciating the fact that Cloud actually cares about somebody, even if that somebody isn't her. On the other hand, in the exact same situation, Aerith loses affection points for Cloud when he shows concern for Tifa.

Visual Novels

Rider in Fate/stay night, judging by Fate/hollow ataraxia. She's clearly pushing Sakura and Shirou together the best she can (very awkward, uncomfortable and dangerous-feeling way) in Heaven's Feel, but in the sequel she's revealed to have something of an attraction to him as well. Oh, and Sakura gets very jealous when Shirou admits that Rider is very beautiful and he likes her. He means it in a completely platonic way, but Sakura's self esteem isn't very good. Interestingly enough, being nice to Rider still gets you Sakura points — and this includes the scene where Shirou says Rider is pretty.

Misha is revealed to harbor one of these in Shizune's route. In a subversion, Misha isn't in love with Hisao... but withShizune.

This may have happened in Lilly's path too. With Hanako developing feelings for Hisao, but choosing to not reveal them since she can clearly see that Hisao is smitten with Lilly.

Riki in Little Busters! starts to develop feelings for Sasami during her route, even though he's trying to help her out with her feelings for Kengo. In his case, it's more out of necessity since he believes that Sasami created the artificial world they're trapped in out of a desire to confess her feelings to Kengo, and that they'll remain trapped until she settles things. The route eventually shows that she isn't the creator of the artifical world like he first thought.

In Rumbling Hearts, Mitsuki does her best to hook Takayuki up with Haruka, only to end up paired with him after the accident. Granted, it's implied that she had a secret crush on him before that but it only fully blossoms after Takayuki and Haruka start going out with her help.

Web Comics

Inverted with Candi. Linda tries to convince Candi to leave her boyfriend, and winds up falling for him during her scheme to break them up to help Candi.

Variation in Homestuck: Jane has a crush on Jake, but when he asks her if she feels that way for him, she panics and says no. He is quite relieved and leaps at the opportunity to have an actual friend to discuss things with, given that all of his other friends have some sort of romantic interest in him. So he ends up confiding in her about how he's pretty sure Dirk has a crush on him and that he's actually considering going along with it. Jane, panicking even more now but desperately trying to be Jake's friend, ends up telling him that's great and even encouraging him to ask him out, berating herself all the while in the process.

Freaking Romance: Zelan initially is a hardcore shipper for Zylith and her best friend Verose. However, things get complicated when he starts to develop feelings for Zylith, and it's implied that the reason he ships them so hard is to avoid his catching feelings.

Web Original

In Keit-Ai, the boy who somehow contacted the alternate universe version of his crush (who's also in love with his own AU self) must cooperate with each other to win the hearts of their other selves. However, DRAMA ensues when he and the AU girl fall for each other instead.

Western Animation

Linus seems prone to these in the Peanuts specials. In Someday You'll Find Her, Charlie Brown, he ends up falling in Love at First Sight with Charlie Brown's "dream girl", completely forgetting that he spent the entire special trying to track her down so that he could introduce her to his friend. It really, really didn't help that the "dream girl" was actually... very similar to Linus. She even had her own Security Blanket!

Star vs. the Forces of Evil has the episode "Sleepover", where it is revealed that Star had unknowingly — even to herself — developed feelings for Marco over the course of their adventures together, despite her regular attempts to make him and Jackie-Lynn Thomas a couple over the previous season and a half. Jackie and Marco getting together causes Star to become so jealous that it causes her magic to go haywire in several episodes. The second season ends with her admitting her feelings for Marco, while Jackie is in the room no less, before moving back home permanently to Mewni.

Community

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